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hexobendine
Sign in to saveHexobendine is a vasodilator that acts as an adenosine reuptake inhibitor.
Chemical data
- Formula
- C30H44N2O10
- Molecular weight
- 592.7 g/mol
- IUPAC name
- 3-[methyl-[2-[methyl-[3-(3,4,5-trimethoxybenzoyl)oxypropyl]amino]ethyl]amino]propyl 3,4,5-trimethoxybenzoate
- SMILES
- CN(CCCOC(=O)C1=CC(=C(C(=C1)OC)OC)OC)CCN(C)CCCOC(=O)C2=CC(=C(C(=C2)OC)OC)OC
- InChIKey
- KRQAMFQCSAJCRH-UHFFFAOYSA-N
- XLogP
- 3.9
- Polar surface area
- 114 Ų
- H-bond donors
- 0
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- cardiovascular disease
via ChEMBL · EBI
Research
141 papers- [Studies on the pharmacokinetics of hexobendine in rats. I. Distribution following i.v. administration (author's transl)].Arzneimittel-Forschung · 1975
- [Review of the literature and report of experiments relating to the coronaroactive drug, hexobendine].Minerva cardioangiologica · 1972
- [Influence of hexobendine, prenylamine and verapamil on the contractile response of isolated rabbit left atria and aortae to calcium (author's transl)].Nihon yakurigaku zasshi. Folia pharmacologica Japonica · 1977
- [Effects of hexobendine on adenosine metabolism and myocardial energy metabolism (author's transl)].Nihon yakurigaku zasshi. Folia pharmacologica Japonica · 1978
- [Clinical experience with N,N'-dimethyl-N,N'-bis-(3-(3',4',5'-trimethoxybenzoyloxy)-propyl)-ethylenediamine dihydrochloride (hexobendine)].Arzneimittel-Forschung · 1968
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 592.3
Show 3 more facts
- chemical formula
- C₃₀H₄₄N₂O₁₀
- canonical SMILES
- CN(CCCOC(=O)C1=CC(=C(C(=C1)OC)OC)OC)CCN(C)CCCOC(=O)C2=CC(=C(C(=C2)OC)OC)OC
- subject has role
- vasodilator agent
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Synthesis
- See also
- References
Hexobendine is a vasodilator that acts as an adenosine reuptake inhibitor.
==Synthesis== Hexobendine can be synthesized starting with a reaction between 3,4,5-trimethoxybenzoyl chloride (1) and 3-chloropropanol (2) to give the corresponding ester, 3-chloropropyl 3,4,5-trimethoxybenzoate (3). The last step involves the reaction between two molar equivalents of 3 with one molar equivalent of 1,2-dimethylethylenediamine (4) completing the synthesis of hexobendine (5). thumb|500px|left| Synthesis of hexobendine
Excerpted from Wikipedia’s “hexobendine” article, available under the CC BY-SA 4.0 licence.